Manufacture of substituted sulphur dyestuffs in substance or on the fiber



Patented Aug. 23, 1932 iuarrse ret st QFF Y' ERWIN KBAMERJDF COLOGNE-DEUTZ, BERNIE-ARI) BOLLWEG, or LEvERKusEu-oN-THE- BHINE, AND LunwIe ZEI-I, or wIEsnoRr-ort'rHE-Rrtmia, GERMANY, ASSIGNORS T0 GENERAL ANILINE WORKS, INC., or NEW YORK, N111, e oolarorvarron or DELA- WARE MANUFACTURE OF SUBSTITUTED SULPHURTDYESTUEFS IN SUBSTANCE OR ON THE FIBER N'o Drawing. Application filed June 21, 1928, Serial in). 287,342, and in Germany iuly l l, 1 927.

The present invention relates to new sulphur dyestuffs and to a process of preparing the same.

In the process hereafter described we use as starting materials the sulphur dyestufis which are obtainable by reacting upon binaphthylenedioxide with a sulphuratlng agent at a temperature between about 170 and 300 C. which process is more fully de-.

scribed in our U. S. Patent No. 1,758,324.

We have found that new valuable substituted sulphur dyestuffs are obtainable by treating the above mentioned starting materials with an alkylating, aralkylating or arylating agent, according to the process described in U. S. Patent No. 688,999

We prefer to carry out the process by dyeing the fibers with the above mentioned starting materials, rinsing the goods and treating them with a solution of an alkylating, aralkylating or arylating agent (for instance,

with a solution of dimethylbenzyl-phenyL' ammonium chloride) at an elevated tempera.- ture and preferably in the presence'of an agent capable of exerting a reducing action and of a small amount of alkali. By working at a lower temperature or without the addition of a reducing agent the development is retarded and it may, according to the agents used in the subsequent treatmententirely fail to take place. The dyeings obtained display very satisfactory fastness to boiling and kier boiling.

Our new dyestuffs yield clear red shades of a quality which was not obtainable hitherto by means of sulphur dyestuffs.

The following examples illustrate'the invention:

Example 1.-The dyeing obtained on cotton with the sulphur dyestulf produced from binaphthylene dioxide by heating the same phenyl-ammonium chloride as the developera beautiful red is likewise obtained. Epichlorhydrin and monochlorhydrin yield duller shades. Vfith the dyestufi obtainable by heating binaphthylenedioxide with sulphur to 240280 G. for several hours and being produced in accordance with Example 1 of our U. S. Patent No. 1,758,824 anddimethylbenzylphenylammonium chloride a clear reddish orange results and with trimethyl-pl1enylammonium chloride a reddish yellow brown. I

EmampZe 2.50 parts by weight of the dyestulf produced from binaphthylene dioxide in accordance with Example 2 of our U. S. Patent No. 1,758,324 are dissolved in water with twice the weight of crystallized sodium sulphide and 20 parts by weight of dimethylbenzylphenylammonium chloride or benzyl chloride are stirred in at the ordinary temperature. zylated dyestufi separates as a red powder, which no longer dissolves in water in the presence of sodium sulphide or hydrosulphide. WVith benzene, nitrobenzene and pyridine deep red solutions are obtained.

The term a sulphur dyestuff derived from binaphthylene dioxide is intended to include the dyestuffs which are obtainable by reacting upon binaphthylene dioxide with a sulphurating agent at a temperature between about 170 and 800 C. i

We claim r v 1. As new products the compounds which are obtainable by treating a sulphur dyestuff obtainable by reacting upon binaphthylenedioxide with a sulphurating agent at a temperature between about 170 and 300 C. with a compound of the group consisting of the alkylating, aralkylating and arylating agents, the said compounds yielding on cotton clear red dyeings being fast to boiling and kier boiling.

2. As new products the compounds which are obtainable by treating a sulphur dyestulf obtainable by reacting upon binaphthylene dloxide with a sulphurating agent at a tem- After a short while the ben-I obtainable by reacting upon 'binaphthylene- V y I v perature between about 17 0 and 300 C. with an alkylating agent, the 'said compounds yielding on cotton clear reddyeings being fast to boiling and kier boiling.

3. As'newproducts the compounds which are obtainable by treating a sulphur dyestufi' dioxide With a sulphurating agent at a temperature between about 17 0 and300 C, With trimethylphenyl ammonium chloride, the said compounds yielding on cotton clear red dyeings being fast to boiling and kier boilmg. 1 L i In testimony whereof We have hereunto set our hands. r

ERVVIN KRAMER. V [L. s.]

BERNHARD BOLLWEG,

[L s] LUDVVIG ZEH. [L. s] 

